Pretend play and bilingualism have rarely been studied together despite having many parallels in quantitative research on theory of mind and executive functioning (EF) in early childhood. Early research on pretend play by Vygotsky theorized pretend play as a form of games-with-rules displaying executive control. Recent studies have mentioned pretense to be integral to development of false-belief and theory of mind in some cases while also coined as possibly an epiphenomenon of other cognitive skills. Bilingualism, has also been related to cognitive benefits in different executive control tasks. Multiple studies relate bilingualism to earlier theory of mind and EF abilities; sparking a similar debate on causality and mechanism as the field of pretense. For this study, pretend play was measured through natural observation. Theory of mind and executive functioning were measured the Sally Anne task, Reed’s Bear/Dragon and the Gift Delay task. We predicted there would be associations between pretense, theory of mind (ToM) and EF. We also hypothesized that bilinguals would perform better on the ToM and EF tasks. Additionally, we predicted differences in pretend play between bilinguals and monolinguals. There was a significant interaction of ToM and age on group and total pretense. Parallel pretense engagement predicted Gift Delay scores above others and no associations were found for the Bear/Dragon task. Bilinguals scored significantly better than monolinguals in the Bear/Dragon task at age four and at age three, their performance was marginally significantly higher in the Gift/Delay Task. There was a significant interaction of language and theory of mind performance on engagement in group pretend play. These results empirically connect both pretend play and bilingualism, to theory of mind and specific domains of executive functioning. They also provide novel data of pretend play in bilinguals and their monolingual populations. The next step called for is longitudinal studies including younger and older age groups.